Hydrochloric Acid → ((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

HRID 906219노트

반응식

HRID 906219 반응식
[OH:1][CH2:2][C@@H:3]1[N:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:6][C@@H:5]([OH:18])[CH2:4]1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([S:8]([N:7]2[CH2:6][C@@H:5]([O:18][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH2:4][C@@H:3]2[CH2:2][O:1][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])(=[O:10])=[O:9])=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 15629267(3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

생성물 1

HCID 15629272((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
10 °C

실험 절차

To an ice-cold solution of 5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (4) (0.45 g, 1.66 mmol) in pyridine (3 mL) is added 4-toluylsulfonyl chloride (1.11 g, 5.81 mmol) in one portion. The temperature rises to 50° C., then the reaction mixture is cooled to 10° C., kept at that temperature for an additional 2 h and then left at room temperature overnight. The mixture is poured into 2N HCl (13 mL). On cooling the compound precipitates out and separated by filtration, washed with cold water (2×5 mL), and dried under reduced pressure to give compound (5) as white solid.

후처리

  1. customrises to 50° C.
  2. waitleft at room temperature overnight
  3. temperatureOn cooling the compound
  4. customprecipitates out and
  5. customseparated by filtration
  6. washwashed with cold water (2×5 mL)
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-88df640c4e7b431ab4c2a3fde45bbe14
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012983B2

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